RO80084B - Process for preparing 4-desacetyl vincaleukoblastine-c-3-carboxyhydrazide derivatives - Google Patents
Process for preparing 4-desacetyl vincaleukoblastine-c-3-carboxyhydrazide derivativesInfo
- Publication number
- RO80084B RO80084B RO97290A RO9729079A RO80084B RO 80084 B RO80084 B RO 80084B RO 97290 A RO97290 A RO 97290A RO 9729079 A RO9729079 A RO 9729079A RO 80084 B RO80084 B RO 80084B
- Authority
- RO
- Romania
- Prior art keywords
- desacetyl
- carboxyhydrazide
- vincaleukoblastine
- derivatives
- preparing
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se prepara 4-desacetil vincaleucoblastin C-3 carboxihidrazide, cu formula generala I: (vezi formula) în care R reprezinta, luat singur, o grupa C1...C3, alcanoil C2...C4, dicloracetil, benzoil sau alchil carbazil C1...C3. R1 reprezinta luat singur, un atom de hidrogen, R si R1 luati împreuna formeaza o grupa alchiliden C1...C3, caracterizat prin aceea ca se trateaza un derivat de 4-desacetil vincaleucoblastina C-3, cu formula generala II: (vezi formula) cu formaldehida, acetaldehida, acetona saupropionacetaldehida, la temperatura camerei, apoi produsul de reactie este eventual supus hidrogenrii, în mod cunoscut.Prepare the C-3 carboxhydrazide of 4-deacetyl vincaleucoblastin of the general formula I wherein R represents, independently, a C1 ... C3 group, C2-4 alkanoyl, dichloroacetyl, benzoyl or C1-6 alkylcarbazyl ... 3. R1 is taken alone, a hydrogen atom, R and R1 taken together form a C1-3 alkylidene group, characterized in that a C-3 4-desacetyl vincaleucoblastine derivative of general formula II is treated: (see formula ) with formaldehyde, acetaldehyde, acetone, and thereafter the sapropionacetaldehyde, at room temperature, then the reaction product is optionally subjected to hydrogenation in a known manner.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/899,032 US4166810A (en) | 1978-04-20 | 1978-04-20 | Derivatives of 4-desacetyl VLB C-3 carboxyhydrazide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO80084B true RO80084B (en) | 1983-01-30 |
| RO80084A RO80084A (en) | 1983-02-01 |
Family
ID=25410402
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO79102377A RO81037A (en) | 1978-04-20 | 1979-04-18 | PROCESS FOR THE PREPARATION OF '-DESACETYL-VINCALEUCOBLASTIN-C3-CARBOXYHYDRAZIDE |
| RO7997290A RO80084A (en) | 1978-04-20 | 1979-04-18 | PROCESS FOR THE PREPARATION OF 4-DESACETIL VINCALEUCOBLASTINE C-3 CARBOXY HYDRAZIDE DERIVATIVES |
| RO79102376A RO81114A (en) | 1978-04-20 | 1979-04-18 | PROCESS FOR THE PREPARATION OF 4-DESACYLVINCALENCOBLASTIN-3-CARBOXYHYDRACIDE |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO79102377A RO81037A (en) | 1978-04-20 | 1979-04-18 | PROCESS FOR THE PREPARATION OF '-DESACETYL-VINCALEUCOBLASTIN-C3-CARBOXYHYDRAZIDE |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO79102376A RO81114A (en) | 1978-04-20 | 1979-04-18 | PROCESS FOR THE PREPARATION OF 4-DESACYLVINCALENCOBLASTIN-3-CARBOXYHYDRACIDE |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4166810A (en) |
| EP (1) | EP0005051B1 (en) |
| JP (1) | JPS54141798A (en) |
| AR (1) | AR228940A1 (en) |
| AT (1) | AT369010B (en) |
| AU (1) | AU527109B2 (en) |
| BE (1) | BE875652A (en) |
| BG (3) | BG33296A3 (en) |
| CA (1) | CA1097629A (en) |
| CH (1) | CH643269A5 (en) |
| CS (3) | CS218583B2 (en) |
| DD (1) | DD143075A5 (en) |
| DE (1) | DE2964130D1 (en) |
| DK (1) | DK147484C (en) |
| EG (1) | EG14867A (en) |
| ES (2) | ES479754A1 (en) |
| FI (1) | FI791286A (en) |
| FR (1) | FR2423495A1 (en) |
| GB (1) | GB2019396B (en) |
| GR (1) | GR69987B (en) |
| HU (1) | HU181431B (en) |
| IE (1) | IE48213B1 (en) |
| IL (1) | IL57168A (en) |
| LU (1) | LU81166A1 (en) |
| NZ (1) | NZ190213A (en) |
| PH (1) | PH14163A (en) |
| PL (3) | PL125470B1 (en) |
| PT (1) | PT69496A (en) |
| RO (3) | RO81037A (en) |
| SU (3) | SU893135A3 (en) |
| YU (1) | YU93179A (en) |
| ZA (1) | ZA791856B (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322351A (en) * | 1980-08-25 | 1982-03-30 | Eli Lilly And Company | Antineoplastic 4'-formylamino and 4'-acetylamino VLB, and derivatives thereof |
| DE3483336D1 (en) * | 1983-03-30 | 1990-11-08 | Lilly Industries Ltd | VINCALEUKOBLASTIN DERIVATIVES. |
| US4667030A (en) * | 1985-06-17 | 1987-05-19 | Eli Lilly And Company | Hydrazide succinimide derivatives of antineoplastic indole-dihydroindole alkaloids |
| US4675400A (en) * | 1985-06-17 | 1987-06-23 | Eli Lilly And Company | Bifunctional derivatives of 4-desacetyl indole-dihydroindole alkaloids |
| US4801688A (en) * | 1986-05-27 | 1989-01-31 | Eli Lilly And Company | Hydrazone immunoglobulin conjugates |
| US5043336A (en) * | 1990-04-03 | 1991-08-27 | Eli Lilly And Company | Cyclic imide derivatives of 4-desacetyl VLB c-3 carboxhydrazide |
| US5043340A (en) * | 1990-04-03 | 1991-08-27 | Eli Lilly And Company | Derivatives of 4-desacetyl VLB C-3 carboxhydrazide |
| DE60231868D1 (en) * | 2001-04-24 | 2009-05-20 | Purdue Research Foundation | FOLAT MIMETICS AND THEIR FOLAT RECEPTOR BINDING CONJUGATES |
| EP2060272A3 (en) * | 2002-05-15 | 2009-05-27 | Endocyte, Inc. | Vitamin-mitomycin conjugates |
| NZ541846A (en) | 2003-01-27 | 2008-12-24 | Endocyte Inc | Vitamin receptor binding drug delivery conjugates |
| US8288557B2 (en) | 2004-07-23 | 2012-10-16 | Endocyte, Inc. | Bivalent linkers and conjugates thereof |
| JP5289935B2 (en) * | 2005-03-16 | 2013-09-11 | エンドサイト，インコーポレイテッド | Synthesis and purification of pteroic acid and its conjugates |
| KR20130113543A (en) * | 2005-08-19 | 2013-10-15 | 엔도사이트, 인코포레이티드 | Multi-drug ligand conjugates |
| US20080280937A1 (en) * | 2005-08-19 | 2008-11-13 | Christopher Paul Leamon | Ligand Conjugates of Vinca Alkaloids, Analogs, and Derivatives |
| US20100087370A1 (en) * | 2007-02-14 | 2010-04-08 | The General Hospital Corporation | Modulation of nitric oxide signaling to normalize tumor vasculature |
| WO2008101231A2 (en) | 2007-02-16 | 2008-08-21 | Endocyte, Inc. | Methods and compositions for treating and diagnosing kidney disease |
| CN104127878A (en) * | 2007-03-14 | 2014-11-05 | 恩多塞特公司 | Binding ligand linked drug delivery conjugates of tubulysins |
| US9877965B2 (en) | 2007-06-25 | 2018-01-30 | Endocyte, Inc. | Vitamin receptor drug delivery conjugates for treating inflammation |
| CA2690943A1 (en) | 2007-06-25 | 2008-12-31 | Endocyte, Inc. | Conjugates containing hydrophilic spacer linkers |
| EP2209374B1 (en) * | 2007-10-25 | 2014-12-03 | Endocyte, Inc. | Tubulysins and processes for preparing |
| WO2011027786A1 (en) * | 2009-09-07 | 2011-03-10 | ニプロパッチ株式会社 | Transdermally absorbable preparation |
| US10080805B2 (en) | 2012-02-24 | 2018-09-25 | Purdue Research Foundation | Cholecystokinin B receptor targeting for imaging and therapy |
| US20140080175A1 (en) | 2012-03-29 | 2014-03-20 | Endocyte, Inc. | Processes for preparing tubulysin derivatives and conjugates thereof |
| EA201590622A1 (en) | 2012-10-16 | 2015-10-30 | Эндосайт, Инк. | CONJUGATES FOR DELIVERY OF MEDICINES CONTAINING NOT MEETING IN THE NATURE OF AMINO ACID AND METHODS OF APPLICATION |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097137A (en) * | 1960-05-19 | 1963-07-09 | Canadian Patents Dev | Vincaleukoblastine |
| US3205220A (en) * | 1961-10-26 | 1965-09-07 | Lilly Co Eli | Leurosidine and leurocristine and their production |
| US3392173A (en) * | 1964-03-09 | 1968-07-09 | Lilly Co Eli | Novel acyl derivatives of desacetyl-vincaleukoblastine and processes for their preparation |
| US3370057A (en) * | 1964-04-27 | 1968-02-20 | Lilly Co Eli | Leurosine |
| US3387001A (en) * | 1964-10-19 | 1968-06-04 | Lilly Co Eli | Novel aminoacyl esters of desacetyl vincaleukoblastine |
| US3887565A (en) * | 1974-05-06 | 1975-06-03 | Lilly Co Eli | Vincadioline |
| US3890325A (en) * | 1974-05-15 | 1975-06-17 | Lilly Co Eli | Leurocolombine |
| US3954773A (en) * | 1974-11-21 | 1976-05-04 | Eli Lilly And Company | 4-Desacetoxyvinblastine |
| US3944554A (en) * | 1975-01-09 | 1976-03-16 | Eli Lilly And Company | 4-Desacetoxy-3-hydroxyvinblastine |
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| US4029663A (en) * | 1975-07-10 | 1977-06-14 | Eli Lilly And Company | Dimeric anhydro-vinca derivatives |
| US4115388A (en) * | 1977-03-30 | 1978-09-19 | Eli Lilly And Company | 3'-Oxygenated derivatives of 4'-deoxy VLB "A" and "B" and related 1-formyl compounds |
-
1978
- 1978-04-20 US US05/899,032 patent/US4166810A/en not_active Expired - Lifetime
-
1979
- 1979-04-17 JP JP4715279A patent/JPS54141798A/en active Granted
- 1979-04-17 PT PT69496A patent/PT69496A/en unknown
- 1979-04-17 PH PH23391A patent/PH14163A/en unknown
- 1979-04-18 BE BE1/9358A patent/BE875652A/en unknown
- 1979-04-18 GB GB7913460A patent/GB2019396B/en not_active Expired
- 1979-04-18 DE DE7979300638T patent/DE2964130D1/en not_active Expired
- 1979-04-18 YU YU00931/79A patent/YU93179A/en unknown
- 1979-04-18 NZ NZ190213A patent/NZ190213A/en unknown
- 1979-04-18 EP EP79300638A patent/EP0005051B1/en not_active Expired
- 1979-04-18 EG EG238/79A patent/EG14867A/en active
- 1979-04-18 GR GR58950A patent/GR69987B/el unknown
- 1979-04-18 AT AT0291279A patent/AT369010B/en not_active IP Right Cessation
- 1979-04-18 RO RO79102377A patent/RO81037A/en unknown
- 1979-04-18 LU LU81166A patent/LU81166A1/en unknown
- 1979-04-18 AU AU46097/79A patent/AU527109B2/en not_active Ceased
- 1979-04-18 RO RO7997290A patent/RO80084A/en unknown
- 1979-04-18 RO RO79102376A patent/RO81114A/en unknown
- 1979-04-19 CS CS792678A patent/CS218583B2/en unknown
- 1979-04-19 ES ES479754A patent/ES479754A1/en not_active Expired
- 1979-04-19 HU HU79EI850A patent/HU181431B/en not_active IP Right Cessation
- 1979-04-19 ES ES479753A patent/ES479753A1/en not_active Expired
- 1979-04-19 PL PL1979230538A patent/PL125470B1/en unknown
- 1979-04-19 CH CH370779A patent/CH643269A5/en not_active IP Right Cessation
- 1979-04-19 DK DK160679A patent/DK147484C/en not_active IP Right Cessation
- 1979-04-19 CS CS807545A patent/CS218584B2/en unknown
- 1979-04-19 FR FR7909874A patent/FR2423495A1/en active Granted
- 1979-04-19 PL PL1979215011A patent/PL119416B1/en unknown
- 1979-04-19 FI FI791286A patent/FI791286A/en not_active Application Discontinuation
- 1979-04-19 CS CS807546A patent/CS218585B2/en unknown
- 1979-04-19 PL PL21591179A patent/PL215911A1/xx unknown
- 1979-04-19 ZA ZA791856A patent/ZA791856B/en unknown
- 1979-04-19 CA CA325,844A patent/CA1097629A/en not_active Expired
- 1979-04-20 AR AR276248A patent/AR228940A1/en active
- 1979-04-20 DD DD79212369A patent/DD143075A5/en unknown
- 1979-04-20 SU SU792759650A patent/SU893135A3/en active
- 1979-04-20 BG BG056469A patent/BG33296A3/en unknown
- 1979-04-20 BG BG056470A patent/BG33297A3/en unknown
- 1979-04-20 SU SU792925606A patent/SU1225490A3/en active
- 1979-04-20 BG BG043323A patent/BG33294A3/en unknown
- 1979-04-29 IL IL57168A patent/IL57168A/en unknown
- 1979-08-08 IE IE795/79A patent/IE48213B1/en unknown
-
1980
- 1980-05-26 SU SU802925605A patent/SU1061698A3/en active
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